


All Hallows Eve

by BeTheCasToMyDean



Category: Supernatural
Genre: Alcohol, Angst, Drinking, F/M, Fluff, Language, Loss of Virginity, Self-Esteem Issues, Smut, Unprotected Sex
Language: English
Status: Completed
Published: 2019-10-20
Updated: 2019-10-20
Packaged: 2020-12-25 00:22:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,123
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21108437
Author URL: https://archiveofourown.org/users/BeTheCasToMyDean/pseuds/BeTheCasToMyDean
Summary: Pairing - Single!Jensen x ReaderRating - NC-17Beta - @winecatsandpizzaWord Count - 2.1kWritten for - @thing-you-do-with-that-thing's Halloween ChallengePrompt - "I should warn you, Princess - the first time tends to get a little messy." Freddy VS Jason (2003)





	All Hallows Eve

You’d been working with the cast for six months now, and every time you laid eyes on Jensen, it always felt like the first time. Initially, you weren’t really excited about having to be one of the main stars’ personal assistant. The thought of waiting on someone hand and foot just didn’t thrill you, but it would have to do. It’s not like you really had a choice back then, seeing as how you moved out here with no money, no place to live, and only the clothes on your back. 

Jensen had no idea that you had such strong feelings for him, and as far as you were concerned he could continue to be clueless. It was easier that way. Misha, on the other hand, practically threw you into his arms every chance he got. Sure, you were thankful for his friendship, but Misha just didn’t understand. There was no way the flawless, bow-legged, Texan would ever be interested in some average mid-western like you. Misha kept trying though, and you had to give him credit in that aspect. 

It didn’t surprise you in the least when he practically dragged you to the annual Halloween party that the cast held. Everyone pretty much went all out on their costumes, but you really didn’t see a reason to put forth the effort. You were just a PA, and probably only five people knew your name. Misha wouldn’t take no for an answer though. He went through your entire wardrobe and made you up like a gothic princess. 

He was right, everyone did go all out. It seemed like the theme this year was dressing up like past characters each actor had played. Jared was dressed as Dean from Gilmore Girls, Misha temporarily dyed his hair and dug up his outfit from playing Paul in the movie Karla, and Jensen was dressed as Tom from My Bloody Valentine. 

Immediately you went for the punch bowl and poured yourself a glass. There was no doubt it was spiked and quite frankly you needed it because seeing Jensen in that mining suit with the fake blood did things to you. Hell, anything he wore did things to you. A vacant table caught your eye and you welcomed the feeling of being able to sit down. The shoes Misha picked out for you were killing your feet. 

As you sipped your punch, your gaze fell on your best friend. He was talking to both Jensen and Jared and every so often their gaze would fall on you. Soon after, Jensen handed his solo cup to Jared and started walking towards you. Any sliver of confidence you had flown out the window as he approached you. It was amazing you could even make out what he said considering your heartbeat was thundering in your ears. 

“Hey Y/N, you okay?”

Your mouth was as dry as the sand in the Sahara Desert as you let your eyes travel up his muscular frame. You were going to kill Misha. He knew you couldn’t talk to Jensen, and he’d thrown you right into the lion’s den. Somehow you were able to manage a response and was surprised it actually made sense.

“Yeah, I uh... I was just taking it all in. You know… my first cast party and all.”

The pattern on your skirt suddenly seemed way more interesting. How could you even look at him when the mere presence of him made your mouth dry? Yeah, Misha was a dead man. Jensen held his hand out to you, and at first, you thought you’d passed out and hit your head or something. Why would a man this flawless want anything to do with you? Wasn’t he seeing someone?

“You wanna go take a walk with me?”

You finally looked up at him, his hand still lingering inches from your own. He looked down at you expectantly, and honestly, he could have asked you to do anything at that moment and you would have done it. Tentatively you slid your hand in his, and the warmth of his fingers made a fire ignite in your belly. 

“I uh… y-yeah sure.”

You caught Misha and Jared’s looks of approval as Jensen led you outside. You shook your head at both of them and did your best to keep your balance in the five-inch heels Misha said you should wear. It confused you when Jensen brought you onto one of the Bunker sets. What an odd place for him to take you. Just as you were about to descend a couple of stairs into the Bunker’s library, your heel got caught and you lost your balance. You shut your eyes tight as you prepared for impact, but instead felt strong arms catch you. Slowly you opened your eyes to see Jensen’s emerald ones staring worriedly at you. 

“Whoa there, sweetheart. That was a close one! Are you okay?”

Truth be told, you had probably sprained your ankle, but in the position, you were in now? Yeah, you were better than okay. Words failed you, so you just slightly nodded as your eyes flitted between Jensen’s eyes and lips. A smirk lifted one side of his mouth as he looked down at you. 

“Good. Because if you were hurt, then I couldn’t do this.”

Before you could even ask what he meant, his eyes were closed and his lips were on yours. Electricity shot through your body as his soft lips caressed your own. All rational thought went out the window as he guided you to the table. Your back gently hit the edge and Jensen held the underside of your thighs as you jumped. His strong arms set you on the table’s surface, his hands cascading up your sides to cradle your face. 

“Jensen…”

As much as you wanted this, you were extremely nervous. Not only were you inexperienced, but weren’t you going to be in trouble for messing up the set?

“Hmmm?...”

His teeth nipped at your bottom lip as he worked at the hooks on your corset. He didn’t seem to be scared of getting caught, but the fact that you were so inexperienced made you pull away from his kiss. Concern filled his eyes as he looked at you. 

“Y/N? What’s the matter? Was I too forward?”

God, this was so embarrassing. How were you supposed to tell him that you were a twenty-seven-year-old virgin? He probably wouldn’t want anything to do with you, and that would be even more humiliating. 

“No, I umm… I’ve just… I’ve never….”

Jensen seemed to understand you through your stuttered response and captured your lips in a chaste kiss. The gentle touch of his fingertips on your cheek comforted you. 

“Y/N, I had no idea. If this is too fast for you, then we don’t have to do this. I just couldn’t resist you any longer. I’ve wanted you since the day you walked on set. Seeing you tonight, in this gorgeous costume was my undoing. I had to kiss you. I had to touch you, but if that’s all I can have, then I’ll be patient. You’re worth the wait.”

Just when you thought he couldn’t get any more perfect, you were proved wrong yet again. You’d wanted to wait for the right person to give yourself too, and before you could even respond to him, you’d made your decision. 

“Jensen…need you…”

In an instant, he was everywhere. His hands worked to get your costume off, his arousal evident in his pants as he ground his hips into yours. Your body was on fire with need as your hands tangled in his short dark locks. Soon your clothes were strewn all over the room, Jensen towering over you on the table as you panted needily below him. 

“You sure about this?  **I should warn you, Princess - the first time tends to get a little messy.** ”

You answered him by capturing his lips with yours. One of his skilled hands snaked between your bodies and slid through your folds with ease. 

“Mmm...so wet already, Y/N. Gotta get you ready for me. Don’t wanna hurt you, sweetheart.”

One of his thick digits pressed against your entrance and your immediate reaction was to tense up. Jensen was quick to capture your lips to distract you. 

“Shh, baby you gotta relax. I won’t hurt you, I promise.”

Once he was able to get one digit in, you became a moaning needy mess. You were meeting every thrust, and when his thumb grazed your clit, you saw stars. Jensen kissed you through your very first orgasm. Your body buzzed from the euphoria as he scissored you open. 

“So beautiful, Y/N. Gonna make you cum on my cock, baby. Wanna fill your sweet little pussy up with my cum. Gonna make you mine, sweetheart.”

Anyone could walk in right now, and you wouldn’t have any willpower to stop. You were putty in his hands. 

“Please, Jay. Need you. Please baby… wanna be yours… make me yours…”

Jensen lined himself up before leaning over you, his lips hovering over your own as he slowly started to slide home. His thick length made you feel so full as your walls stretched around him, your breaths coming in thick pants.

“Shh. I got you, baby. Just relax for me. Breathe for me, Y/N. In and out. That’s it. It won’t hurt for very long.”

If it wasn’t for him talking you through it, you didn’t think you would have been able to take all of him. Jensen filled you to the hilt, his balls resting against your ass. After a couple of minutes of silence, your eyes opened to see Jensen looking lovingly into your eyes. 

“That’s it, there’s my girl. You’re doing so good, baby. Such a good girl, Y/N.”

Your nails dug into his biceps as you nodded up at him. 

“Please, Jay...need you to move…”

Ever so slowly, he pulled almost all the way out. Your walls clenched around nothing as he pushed back into you just as slow. His lips captured yours in a sweet kiss as both your moans filled the room. Jensen built up a slow punishing rhythm, his tongue licking along your bottom lip requesting permission which you immediately granted. He tasted of cinnamon and spices, and that only added to the familiar heat beginning to resurface in your lower abdomen. 

“Fuck, Y/N… you’re so tight, baby… so beautiful…” 

“Oh god, Jay… Ohhhh…… please…. I wanna cum again.. Please…”

Somehow, Jensen was able to maneuver you both so that he was sitting in one of the chairs with you straddling his lap. He felt so much deeper at this angle, and it made your eyes roll back with pleasure. You felt yourself clench around him, and he growled. 

“You keep that up, and I won’t last Y/N. You’re so perfect, so good at milking my cock, baby. Think you can ride me, Princess?”

All you wanted to do was please him. You wanted to show him that you knew a thing or two, even though you’d never done this before in your life. Basic instinct took over, and you placed a hand on each of his shoulders and began to rise and fall. His hands came to rest on the underside of your ass to help lift you up as your cries got louder. 

“Ah! Jensen… fuck baby! I… I think I’m gonna… Oh god… yes right there….”

His blunt nails raked down your bare back as your walls began to flutter around him. You threw your head back as another white-hot orgasm took over your body. Jensen cried out and rested his head in the crook of your neck as he pumped rope after thick rope of his cum into your womb. 

Minutes later, he lifted you off him and carried you to Dean’s room in the bunker. He covered you both with a blanket, peppering your skin with lazy kisses. 

“You did so well, Y/N. You’re amazing.”

He groaned as your nails scratched at the small hairs on the back of his neck. 

“I’ve never felt that good in my life, Jay. Thank you for being so gentle with me.”

His arms snaked around you, his chin resting on the top of your head as you cuddled against him. You needed to thank Misha too. If he hadn’t insisted you come tonight, then this probably wouldn’t have happened. 

“I should be thanking you, Y/N. I haven’t been this happy or felt this complete in a long time.”

You felt your eyes droop as you snuggled against his chest. The party remaining forgotten as you fell asleep in Jensen’s arms. 


End file.
